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Showing Compound 2-Methoxyestradiol (FDB022021)

Record Information
Version1.0
Creation date2011-09-21 00:07:07 UTC
Update date2015-10-09 22:30:04 UTC
Primary IDFDB022021
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Methoxyestradiol
Description2-Methoxyestradiol (2ME2) is a drug that prevents the formation of new blood vessels that tumors need in order to grow (angiogenesis). It is derived from estrogen, although it binds poorly to known estrogen receptors, and belongs to the family of drugs called angiogenesis inhibitors. It has undergone Phase 1 clinical trials against breast cancers. Preclinical models also suggest that 2ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis. The CAS name for 2ME2 is (17 beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol. It also acts as a vasodilator. [HMDB]
CAS Number362-07-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,3,5(10)-ESTRATRIEN-2,3,17-BETA-triol 2-methyl etherChEBI
2-Hydroxyestradol 2-methyl etherChEBI
2-Methoxyestradiol-17betaChEBI
PanzemChEBI
1,3,5(10)-ESTRATRIEN-2,3,17-b-triol 2-methyl etherGenerator
1,3,5(10)-ESTRATRIEN-2,3,17-β-triol 2-methyl etherGenerator
2-Methoxyestradiol-17bGenerator
2-Methoxyestradiol-17βGenerator
2-(Methyl-11C)methoxyestradiolHMDB
2-Methoxyestradiol, (17alpha)-isomerHMDB
2-MethoxyoestradiolHMDB
2-Methoxyestradiol-17 betaHMDB
2ME2HMDB
(17Β)-2-methoxyestra-1,3,5(10)-triene-3,17-diolHMDB
(17beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diolHMDB
2-Hydroxyestradiol 2-methyl etherHMDB
2-Methoxy-e2HMDB
2-Methoxyestra-1,3,5(10)-triene-3,17β-diolHMDB
2-Methoxyestra-1,3,5(10)-triene-3,17beta-diolHMDB
2 MethoxyoestradiolHMDB
(17 beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diolHMDB
2 Methoxyestradiol 17 betaHMDB
2 MethoxyestradiolHMDB
2-MethoxyestradiolHMDB, ChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.0097 g/LALOGPS
logP3.7ALOGPS
logP3.59ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.37 m³·mol⁻¹ChemAxon
Polarizability35.2 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H26O3
IUPAC name(1S,10R,11S,14S,15S)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
InChI IdentifierInChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
InChI KeyCQOQDQWUFQDJMK-SSTWWWIQSA-N
Isomeric SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3
Average Molecular Weight302.4079
Monoisotopic Molecular Weight302.188194698
Classification
Description Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-hydroxysteroid
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS2-Methoxyestradiol, 2 TMS, GC-MS Spectrumsplash10-016s-2792200000-4c8c5cfcb17a537e5130Spectrum
GC-MS2-Methoxyestradiol, non-derivatized, GC-MS Spectrumsplash10-016s-2792200000-4c8c5cfcb17a537e5130Spectrum
Predicted GC-MS2-Methoxyestradiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dr-1190000000-c0b6f1d0f5e462b22c79Spectrum
Predicted GC-MS2-Methoxyestradiol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00lr-2114900000-32b6a1587678bf94533fSpectrum
Predicted GC-MS2-Methoxyestradiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Methoxyestradiol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Methoxyestradiol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Methoxyestradiol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Methoxyestradiol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Methoxyestradiol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-51addcf0be873acf45682012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-9189876ead18b5520cfc2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-0900000000-c60cd007c37d58b43c6f2012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0197000000-e6452081e4d95484a78e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0592000000-f334c69fd08d4a2989982017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-3690000000-d1b1dc06b52f7fe1f05c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-2e5aedfaa3bc522112af2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0069000000-2106698fbc9b5342a9b12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-0090000000-299f520e49dfbd52ed632017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-4360bacaf95498925fe52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-b5cab14cef0400c3f7b62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0090000000-98926d2ec85f54a466322021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-1d8e847a4bc26e5c12122021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fbi-0594000000-53e59c7ba30eb8c1eb1e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056v-3930000000-32bdd6b4eab8d995c6412021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID59788
ChEMBL IDCHEMBL299613
KEGG Compound IDC05302
Pubchem Compound ID66414
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00405
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDESM
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID2-Methoxyestradiol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B10UGT2B10P36537
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-8UGT1A8Q9HAW9
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 1-10UGT1A10Q9HAW8
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 1-7UGT1A7Q9HAW7
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference